The present inventor previously proposed a process for converting diethylzinc to an aldehyde by an asymmetric reaction using various 3-amino-2-hydroxybornane derivatives of exo or endo form as a ligand as reported, e.g., in The Chemical Society of Japan, Lectures (II) of the 58th Spring Meeting, Lecture No. 3 IIID 16, p. 1602 (1989) and the 2nd International Conference of Hetero Atomic Chemistry, Abstracts, p. 129, Lecture No. PA-44 (1989).
3-Amino-2-hydroxybornane derivatives used in the process proposed are represented by formula: ##STR2## wherein R represents a methyl group, a cyclohexylmethyl group, a 1-methylpyrrolidinylmethyl group, a diphenylethyl group, or a thenyl group. A compound having the above formula wherein R represents a furfuryl group, a 1-methylpyrrolylmethyl group or a benzyl group is unknown and novel.
On the other hand, 1,4-addition to 2-cyclohexenone by an organometallic reagent using (-)-sparteine, 1,4-bis(dimethylamino)-2,3-dimethoxybutane,1,2,3,4-tetramethoxybutane,or 1,4-bis(dimethylamino)-2,3-bis(2-N,N-dimethylaminoethoxy)butane, etc. as a ligand has been reported as an asymmetric Michael reaction distinguishing the enantioface as described in Fusai Gosei To Kogaku Bunkatsu No Shinpo, Kagaku Zokan, No. 97, pp. 44-45, Kagaku Dojin (1982). However, there has been reported no case in which a 3-amino-2-hydroxybornane derivative is used as an asymmetric ligand.
Further, it has been proposed to synthesize muscone by reacting 2-cyclopentadecenone with a methyl Grignard reagent in the presence of cuprous chloride and diethyl ether as described in Journal of Organic Chemistry,Vol. 36, No. 26, pp. 4124-4125 (1971) This process, however, produces only racemic muscone.